Executive Assistant & Accountability Partner (Full‑Time, Remote, ET Hours)
About the role We are seeking a college‑educated, high‑judgment Executive Assistant to partner with a CEO and spouse across work and family operations. This is a 40 hrs/week, long‑term role in Eastern Time (ET). You will run complex calendars and travel, keep our “family operating system” tight, act as a gentle accountability coach for both principals, and prepare bill payments within a clear approvals workflow. We’re looking for someone who leads up—proactive, thoughtful, and comfortable prompting us toward better outcomes. What you’ll own Calendar & inbox mastery: Orchestrate a fast, high‑stakes calendar; defend focus time; draft agendas/briefs; triage email. Travel end‑to‑end: Book smart, flexible itineraries (US/UK time zones), leverage card/travel benefits, manage changes. Family OS (Google: Maintain a living hub of contacts, vendors, renewals, school/athletics dates, medical appointments, SOPs. Accountability coaching: Weekly 15‑min 1:1 with each principal to set 3 personal goals and one weekly “keystone,” Mid‑week nudges, Friday 15‑min readout (progress, blockers, next experiment). Vendors & projects: Coordinate household vendors; manage multi‑week projects with crisp updates and measurable checkpoints. Bill‑pay prep (simple & safe): Draft bills in BILL (formerly Bill.com) with role‑based approvals (you prepare; principals approve), Use 1Password for shared credentials (least‑privilege access), Use Privacy virtual cards for subscriptions/incidentals (merchant‑locked, spend caps). Documentation & improvement: Keep SOPs current; propose improvements; measure what matters. You bring Bachelor’s degree from an accredited university. 5+ years supporting a founder/CEO or senior executive (remote OK). Exceptional written communication and executive judgment. Demonstrated ability to lead up—anticipate needs, push back diplomatically, and improve the system. Tool fluency: Google Workspace, BILL, 1Password, Privacy (or quick to learn equivalents). Comfortable coordinating across US/UK time zones. Located anywhere and able to work ET hours. Nice to have Exposure to coaching principles (e.g., ICF‑style accountability, active listening), project tools (Asana/ClickUp), and travel perks (e.g., Amex FHR/Virtuoso). Compensation & terms Salary Retention bonuses Performance bonus opportunity tied to measurable outcomes (calendar health, on‑time deliverables, SLA). How to apply Please submit the following.Do not use AI to generate: Resume (1 page) and 150‑word note on a complex calendar or travel problem you solved, A short writing sample you’re proud of (max 300 words), We’ll invite selected candidates to a 15‑minute cognitive assessment and a paid practical (60–90 min: inbox triage, ET calendar rebuild, and a BOS↔LHR travel brief). Trust & background Finalists will complete reference checks, a background check, and sign an NDA.